Loudon Wainwright III in Bend

Singer-songwriter plays Tower Theatre

By David Jasper / The Bulletin

When Loudon Wainwright III released “Older than My Old Man Now,” the 22nd studio album of his 45-year career, he was 65.

He turned 66 in September.

At that age, even the least contemplative among us might pause to think about mortality. For a singer-songwriter known for his candor — whose “old man” died at age 63 — facing up to the fate that awaits him is just part of the job description.

“I have called it ‘the double d’ — death and decay,” he told GO! Magazine by phone last week as he prepared for a West Coast tour that brings him to the Tower Theatre on Tuesday (see “If you go”). Singer-songwriter Dar Williams, promoting her seventh studio album, “Promised Land,” will open the show.

“I’m of that age where one might think about it a bit,” Wainwright said. During the interview, he sounds pretty lighthearted about this whole business of dying. Likewise on the album, wherein he wades through the miasma of late life, facing subjects such as medicine (“My Meds”) and decreased libido (“I Remember Sex”) with his trademark humor and eclectic approach to folk music.

Wainwright has said of “The Here and the Now,” the 15-song album’s jazzy opener, “Contemporaries of mine have recently taken to writing memoirs and autobiographies. I decided I would try to tell the story of my swinging life in a 3 1/2 minute song.”

He told GO!, “I had a collection of songs that it seemed like, every single one of them, in one way or another, dealt with the topic. So I threw caution to the wind ... my producer Dick Connette (and I) just decided to focus on that particular subject, and I think we did.”

They were conscious of not making things too heavy.

“Certainly, with that subject, it needs a light touch. Otherwise, you just get people bummed out for 50 minutes or however long the record lasts,” he said. “The idea being, we’re going to do a record about death and decay, but it would be entertaining.”

To lighten matters further, friends and family participated in the recording sessions. A bevy of musician friends turn up on the record, including Ramblin’ Jack Elliott, Chaim Tannenbaum, Dame Edna Everage and Chris Smither, as well as jazz guitarist John Scofield.

All four of Wainwright’s children, including Rufus, Martha, Lucy Roche and Lexie Kelly Wainwright, appear on the album, along with two of their three mothers, Suzzy Roche and Ritamarie Kelly. (Rufus and Martha’s mother, the talented singer Kate McGarrigle, died of cancer in 2010 at age 63.)

Playing music with his offspring “is always fun. I’ve know them for their entire lives,” Wainwright said with a chuckle. “I’ve done shows with them over the years. They also happen to be really talented singers in addition to their other gifts. It seemed logical to bring them on board.”

Wainwright also reads passages from his father’s work as a Life Magazine columnist, including one Loudon II wrote about his dad dying, to start the title track. Over acoustic guitar and harmonica, Wainwright sings, “I guess that means I kicked his ass/ But just ’cause you’ve survived that don’t mean that mean you feel alive / and your demise will come to pass.”

Growing up, he experienced three formative events for his future as a singer-songwriter: In 1956, he bought his first Elvis record. In 1960, he started playing guitar, and in 1962, he saw Bob Dylan for the first time.

Before he trained his creative eye on a professional music career, Wainwright studied drama at Carnegie Mellon University beginning in 1965. A self-proclaimed hippie, he dropped out in 1967 to head to San Francisco. “I was a young guy just out to have a good time and hitchhike,” he said. “Then I slipped back into music.”

After his dad bailed him out of the Oklahoma jail where he did a five-day stint for pot possession, Wainwright began working odd jobs to pay him back. He also began writing songs, which would eventually pay a lot better than movie house janitor or boatyard barnacle scraper.

He wrote his first song, “Edgar” in 1968, about a Rhode Island lobsterman. He signed to Atlantic Records in 1969, and released his first album in 1970.

“My father was a journalist you know, and I think I have kind of an almost journalistic eye when it comes to writing songs,” he said. “I can get very specific and minute.” And colorful, as evidenced by his biggest hit, “Dead Skunk,” a top-20 song in 1972 on which he sings, “Take a whiff on me, that ain’t no rose / roll up your window and hold your nose.”

Wainwright would return to acting in 1975 with a recurring role on “M*A*S*H” as a singing surgeon, and he’s had roles in movies directed by Tim Burton, Judd Apatow, Martin Scorsese and Cameron Crowe.

But acting is merely “a pleasurable break from the singing and guitar-slinging. I enjoy it when it happens, and look forward to my next acting job,” he said.

Music is the Grammy-winning Wainwright’s mainstay. And whether he’s joking about Cialis in a piano ditty or revealing the ugly impact crater of divorce, Wainwright’s all about honesty — even if it makes people squirm.

“When I write a song, usually the process is, if I’m interested and I think it’s good, I go out and perform it for people. See if that works, see if it has any effect,” he said. “One of the effects I’m always looking (for) is to make people feel a little uncomfortable, so an audience’s discomfort doesn’t necessarily rule out a song.”

His newest song, he said, is about double parking in his home of New York City and waiting for the street sweeper to go by.

“Part of the fun for me is to write about anything, or write about very mundane, almost silly things, and somehow engage a group of people who (experience) that song,” Wainwright said.

Those who catch his set Tuesday can expect to hear that one, along with others from “Older than my Old Man Now,” from the forever-pensive singer. (Well, maybe not quite forever.)

“It’s been a funny little career,” he said. “I suppose I’d like to be a little more famous than I am. But I enjoy my anonymity, too. God, it must be tough to be Bob Dylan. I don’t envy that thing of not being able to walk down the street.”